


Sugar Please

by fluffy_miracle



Category: Supernatural
Genre: Accidental Voyeurism, Alternate Universe - Beauty and the Beast Fusion, Alternate Universe - College/University, Alternate Universe - Lawyers, Alternate Universe - Sugar Daddy, Angst, Angst with a Happy Ending, Beauty and the Beast Elements, Bossy Gabriel, Boys In Love, College, College Student Sam Winchester, Curses, Dom Gabriel, Emotional Hurt/Comfort, Eventual Gabriel/Sam Winchester, Eventual Happy Ending, Fights, Florist Castiel (Supernatural), Fluff, Fluff and Angst, Gabriel (Supernatural) is Bad at Feelings, Gay Gabriel (Supernatural), Heartbreak, Homophobia, Homophobic Language, Hurt/Comfort, In Control Gabriel, Internalized Homophobia, Kinks, Lawyer Gabriel (Supernatural), Lawyer Lucifer (Supernatural), Light Dom/sub, Love, M/M, Mechanic Dean Winchester, Money, Nudity, Partial Nudity, Poor Sam Winchester, Possessive Gabriel, Professor Lucifer (Supernatural), Sabriel - Freeform, Sam Winchester is Bad at Feelings, Sam is in Law school, Sex, Slow Build, Slow Burn, Strangers to Lovers, Stripping, Sugar Daddy, Sugar Daddy Gabriel, Uncomfortable Sam Winchester, broke, but not in a bad way, controlling Gabriel, everyone is bad at feelings, money issues
Language: English
Status: In-Progress
Published: 2019-03-30
Updated: 2019-09-25
Packaged: 2019-12-26 20:44:34
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 7,286
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18289904
Author URL: https://archiveofourown.org/users/fluffy_miracle/pseuds/fluffy_miracle
Summary: Broke, struggling law student Sam Winchester  finds out about a program that helps students like him survive life while scholarships pay for tuition. Sam just wishes that his friend had let him know he was calling and applying to receive a sugar daddy. With Beauty and the Beast themes underlying, Sam finds his life changing dramatically when mysterious Gabriel Milton accepts his application. Forced to move in with the man and quit his two jobs, Sam stresses with feeling lost and out of control, lashing out at the man who he had to ask to save him.Gabriel Milton, said mysterious sugar daddy, would normally fire a sugar baby for such behavior, but as it is, he is far too intrigued with Sam Winchester to let him go yet. When he steps up his game and goes the extra mile to help Sam out, he starts to see who the law student really is and why it is so hard for him to Let Gabriel help him, even when he desperately needs it. Two lonely men for two different reasons start to find out those reasons maybe don't matter as much as they thought they should anymore.Cue "Maybe there is something there that wasn't there before."





	1. Mr. Milton

Sam Winchester, law student extraordinaire, was feeling stretched. He was working two jobs, was enrolled in Stanford law school, and was barely making his classes, let alone making ends meet. So when a former classmate told him to inquire with a Mr. Gabriel Milton about a position with the raving recommendation that this was the only way they survived their academic career and ‘the work wasn’t that bad at all,’ Sam did just that. And now, sitting in a leather chair, surrounded by an expensively if not eccentric-ly decorate office, Sam was wishing he had done a little more research on what the open position was for. As it would turn out, Gabriel Milton was something of a sugar daddy looking for a sugar baby.

“I was surprised to receive your impressive resume.” Said Mr. Milton smirked from across the desk as Sam. “You don’t seem like the type I normally get in here.”

“I’m not.” Sam replied honestly, swallowing hard. “I’m not going to make rent this month and if I get kicked out… if I can just survive this next year then everything will be better.”

“So you want to be a lawyer?”

“Yes.” Sam responded, feeling like this was an actual interview now.

“Why?”

“I want to help people, especially those who have no one to fight for them.” Mr. Milton snorted, glancing down at the paper he kept moving around his smooth desk with his index finger.

“Lawyers don’t help people, kid, but you’ll find out soon enough. It says here you have an internship coming up… how are you going to juggle the demands of an internship and the demands that I will give you?”

“I’ll meet those demands.”

“You’ll need to quit the two jobs you’re working now.” Mr. Milton moved on down the paper.

“But I need the money—“

“You won’t need the money, Sam. Can I call you Sam? I take very good care of my sugar babies.”

“You have more than one?”

“I keep about five or six.”

“Why?”

“Because they’re usually students and because I like variety. I can afford variety.” Mr. Milton smiled. “Anyway, if I’m interested, my secretary will call you tonight.”

“Thank you for your time, sir.”

“Please,” Mr. Milton smiled, “call me Gabriel. You might as well since we might be intimate.”

“Thank you again.” Sam bobbed his head, avoiding calling the man by his name. It seemed too soon to be so familiar, even if he did have a point.

“Make sure you send a current photo to my secretary.” Sam had forgotten about adding a current shirtless photograph to the resume he had given the man. For someone who was shorter than him by a foot, Mr. Milton had a very imposing presence.

“You’re very open about being—“ Sam trailed off, not wanting to offend his potential employer.

“A sugar daddy?” Gabriel laughed, not cruelly but also not that kindly either. “I’ve worked hard to get where I am, Sam. I won’t be ashamed or guilty of my pleasures. I’ve earned them.”

“I’m sorry,” Sam ducked his head down, “I really didn’t mean to offend. I’m not really sure about all the language to use.”

“I expected a future lawyer to do his research.”

“I’m sorry.” Sam flushed, his stomach sinking. “It’s been a hard week and well, I’m- I’m desperate.” Gabriel Milton regarded him out of the corner of his eye before he waved him out of his office.

“Thank you again for coming. You’ll know my decision by seven o’ clock tonight.” Sam glanced at his watch. That was five hours and twenty-four minutes away. It was going to be a long day, even though he wasn’t sure if he wanted this job.

 

* * *

 

At 5:35pm, Gabriel Milton went over Sam’s resume with a critical eye, then he went over the notes he took after the awkward interview, and lastly, he studied the photos his secretary had brought in before she left for the evening.

“This a new one?” One of his coworkers stopped by.

“I don’t know. He was awkward and stiff.”

“Maybe you could teach him to relax, I mean, he’s gorgeous.”

“I don’t think even I could teach this one to relax. He was kind of judgy.”

“Well, it’s up to you.” They shrugged. “Maybe send him my way if you don’t take him.” They smiled, knowing all too well that Gabriel would take Sam on if just to not share him. “I’d teach him to relax.” They added wistfully. “Goodnight, Gabriel.”

“Goodnight.” Gabriel looked back at the picture and then at the clock. 6:24. Kevin would be here soon. He could call Sam early and let him know his decisions. Gabriel was ready to call it a night. He had a busy weekend planned, and Kevin Tran, was just the beginning.

 

* * *

 

Sam jumped when his phone went off, falling over his books in his hurry to pick his phone up.

“Hello??” He said breathlessly into the receiver.

“Hello, Sam.” The voice on the other end was none other than the polished potential future employer. “I’ve reviewed your application thoroughly. Thank you for submitting a photo in such a timely manner.”

“Sure, I mean, you’re welcome.” Sam stammered. This whole situation flustered him so much. He hoped Mr. Milton didn’t mind his nervousness. He had lost more over less though.

“Sam, relax.” There was an amused tone. “You got the job. Please join me for dinner at 6pm on Sunday at my mansion. I will text you the address.” Sam’s cell buzzed and he pulled it down to glance at the address that popped up. “Did you get it?”

“Yes, sir.” Mr. Milton laughed at his formality.

“While I don’t mind being called sir in certain contexts,” and didn’t that comment spike Sam’s anxiety, “you can just call me Gabriel.”

“Gabriel.” Sam tried the name out, disliking how intimate it felt on rolling off his tongue.

“That’s better.” Mr. Milton’s smile could be heard through the phone. “See you Sunday.”

—-

“Is that the best suit you own?” Sam blinked like a deer caught in the headlights of an oncoming car.

“Yes, sir, Mr. Milton.” At Gabriel’s raised eyebrow, he all hit spat out the older man’s name. “Yes, Gabriel.”

“You’re uncomfortable.”

“I—no.”

“You are.” Gabriel leaned forward, studying him. “I already know you are poor, what could you possibly be ashamed of?”

“It’s stupid.” Sam muttered, sucking down the sparkling beverage in his champagne flute, noting that it was non-alcoholic, sparkling apple juice as he swallowed.

“I need you with a clear mind.” Gabriel nodded towards the flutes. “I rarely drink myself.”

“Why?”

“I prefer to face my problems head on.” Gabriel reached for his own glass. “Now tell me.”

“I don’t like calling you Gabriel; I don’t feel like I know you well enough to be so familiar with you.”

“Thank you for telling me.” Gabriel murmured instead of mocking him like Sam expected him too. “You can call me whatever you feel comfortable with Sam, except for sir. That’s only for when you want me to strap you down to a bed and have my wicked way with you.” He grinned as Sam swallowed hard. “But we may never get to that level and that’s perfectly fine with me.”

“Don’t you sleep with us, Mr. Milton?”

“Boardroom etiquette it is, Mr. Winchester.” Gabriel deepened his voice for the line. “I don’t, not with all, only the ones who came on to me first. In fact, before you came, one just resigned from their position. They were one that I slept with quite regularly, so now I only have one other one that I have any kind of sexual relations with.”

“Why not all of us? You’re in a position to demand it.”

“I still think you haven’t done your research, Mr. Winchester. It’s my duty to take care of you and it’s your duty to keep me from feeling lonely.”

“You could have anyone you want.” Sam laughed in shock. “What could I give you that you couldn’t not buy yourself?”

“But I have bought you.” Gabriel raised an eyebrow. “As your employer, I have purchased your time, and let me warn you, that while I don’t feel lonely around you, I do feel annoyed. I might have to find a quiet job for you, have you walk around my office gagged and shirtless. I think the whole office would enjoy that.”

“That would be humiliating.” Sam remarked bitterly.

“So I’ll remove the gag, but only if you keep your mouth shut. Also, pack your things. I saw your apartment, it looks awful, I can’t having you make me look bad. You’ll be moving in here with me.”

“I have classes to attend!”

“And you will.” Gabriel rolled his eyes. “Seriously, Sam, do your research and practice keeping your mouth shut. You’re embarrassing yourself.” That stung, doing the trick in shutting up the younger man. He looked positively wounded, but was finally, blissfully silent.


	2. First Day

**Notes for the Chapter:**

> Okay, so it seems that it was down between author's choice and regular world. I almost went A/B/O, but as I want to do this story justice, I listened to the feedback that there is enough going on right now. Thank you all for telling me what you thought, I really appreciated it! I hope you like this next chapter.
> 
> -fluffy

Sam packed his bags slowly, each moment feeling like an eternity. If he was being honest, he wanted to take his sweet time getting ready, put off the inevitable for as long as he could. He had quit his jobs, he had amended his class schedule for next semester as Mr. Milton had requested. He couldn’t actually be going through with this, could he? He couldn’t be moving in with this man that he barely knew. There was the contract, but he wasn’t sure quite how that protected him. Fuck. Mr. Milton was right. He needed to do his research.

Putting off packing, Sam pulled his laptop out of his bag and started to research what exactly all of this meant. Three hours later, he closed his laptop with a heavy sigh. This seemed legit. Mr. Milton definitely was legit, otherwise Kevin Tran wouldn’t have recommended the man. Sam wondered if Kevin’s upcoming graduation was why he left Gabriel’s employ, or else the cushy new job he got offered at some fancy lab. His phone rang, and he cursed as he glanced at the clock. He was supposed to be at the Milton mansion by now.

“Hello?”

“Sam.” It was Mr. Milton. “Are you lost?”

“I’m sorry, Mr. Milton, I, uh, I lost track of time.”

“Were you researching at least?” There was a faint trace of humor in Mr. Milton’s tone that relaxed Sam ever so slightly. 

“Yes, sir, I mean--”

“Relax.” Mr. Milton cut him off. “Meet me tonight for dinner at my place. Three more hours, kid.”

“Thank you, Mr. Milton.”

“No problem. See you later.” Gabriel disconnected the phone then and there. He tossed his phone on his plush couch. He had the day off, he might as well watch some porn, especially since Kevin cut him off. Ah, Gabriel wished him well, it was just, well, it had been nice to have a connection as strong as he and Kevin had. Had. Whatever. Gabriel texted for a nice, mixed cocktail with an umbrella included. He’d drink and wank off, be ready for calming Sam Winchester’s fucking nerves.

\---

Sam finished packing, and then spent the last hour googling Gabriel Milton. He was a lawyer, a really good one at that. Sam wished he had known that going in. No wonder Mr. Milton had expected more of him as a law student. An hour researching and he only found out what Gabriel did to make money and how most people contacted him to be a sugar daddy. It wasn’t a bad profile picture.

He loaded his stuff into the taxi, hoping that Gabriel would foot the tab for the car since he didn’t have the money to make it all the way to the nice area in which Gabriel lived, on the opposite side of the city. When they made it, the taxi driver looked annoyed that Sam made him wait. 

“Uh, Mr. Milton,” Sam glanced back at the waiting taxi, “Can I-- I’m short--”

“I’ve got it.” But Sam didn’t miss how Mr. Milton frowned almost imperceptibly. Interesting.

“Thank you, I’m sorry, I thought I’d have enough, it’s a long way and I was short, I’m sorry, I won’t ask again.”

“You are rambling.” Gabriel pulled off a bill from a thick wad of cash that was in his pocket. “Go give this to him and tell him to keep the change for his troubles, okay?” Gabriel headed back into his large house, and Sam watched him go with a knot in his stomach. He felt dread at moving back in with this man who he still knew next to nothing about. He did as he was told though, giving the money to the man and thanking him. He turned to see a couple men coming out of the house. They carried all his shit inside without a word, up to his room that he hadn’t seen yet. The taxi driver whistled low, looking Sam over like he was some kind of whore, and didn’t Sam feel kind of like one.

The taxi driver drove off with one last judgmental look and Sam headed inside, knowing it was time to stop hiding from his new reality. If he wasn’t so fucking desperate… he wouldn’t be here, but here he was. Before he had applied to this, he was about to fired from one of his other jobs for being late, and if he lost that job, he would have lost his crappy apartment as well since he needed both jobs to pay for rent. That didn’t account for the fact that anything extra he sent home to Dean to help out back home, even if Dean didn’t know it was him. Things had been rough for his big brother, and sending Sam to college had put him back even further. Sam just wanted to help, but now, he couldn’t even help himself.

“I am sorry.” Sam slipped inside and took the seat across from Gabriel. “I’m not trying to be that person.”

“A user?” Gabriel raised an eyebrow, deigning finally to look at Sam. “Don’t worry about it, Samuel. I’ll give you a generous allowance, I’m sure you won’t overspend it because you won’t get a dollar more.” 

“I’m not that person.” Sam lowered his head, reminding Gabriel of a spanked puppy.

“I hope I will be granted the clarity to see that in the future. Work starts tomorrow. I think I am going to go through with the day in the office, shirtless.”

“Please don’t.”

“I am not here to make life easier for you, kid.” Gabriel snorted. “I want to see you shirtless when I look up from my desk tomorrow. If you behave, you can wear a shirt in and out.”

“Fine.” Sam glared. “But let it prove, I’m not after your money like that.”

“But you are after my money.”

“I just want my wages.” Sam stuck his jaw out. “No more, no less.” Gabriel leaned back in his chair, studying him.

“Fine.” He waved his hands in the air. “Let’s do this.”

\---

The room was nice, nicer than any room Sam had ever seen. That wasn’t too shocking since home was a double-wide that was falling around the family of four. Home had been a crappy apartment that was infested with cockroaches. This plush bed that he sank into, curling around soft pillows, was more comfortable than all of the beds he had slept on put together. He unpacked and went to bed, dreading what would happen the next day.

\---

The next morning Sam was grumpy, but true to his word. They drove together to Gabriel’s office, Sam fully dressed attracting enough attention. He was an attractive young man and for now, he was Gabriel’s. If he didn’t quit after today anyway.

Gabriel had fed him well, made him breakfast himself although he had the help that could have done it instead. He bought him coffee and a snack. And then they made it to the high rise. Sam was given a comfortable chair next to the wall of window that looked out over the city. 

“Nice view.”

“It’s about to improve.” Gabriel didn’t even look at him when he said that, rifling through his papers. “Feel free to do your homework.” Gabriel handed over a laptop that was worth more than a couple months’ rent, way better than his trusty, but beat up one that he had now. “It’s yours as a welcome gift to the job. Now shirt off.” He looked up with a smirk as Sam scowled, sliding the tie out of his shirt collar before he started on the shirt buttons. He didn’t have to look to the window looking into the office to know there was a crowd there.

 

“This has got to be against some kind of HR rules here.”

“Probably, but you agreed, so it’s not harassment.” Gabriel shrugged. “Shirt off.” Sam pulled his arms out of the light blue sleeves, taking care to fold the shirt carefully and then the tie. These clothes were the only nice ones he had.

“It is still some kind of harassment.”

“It’s only for today, Sam.” Gabriel was already working on something, not even oogling Sam like Sam expected. He hadn’t even looked once at Sam’s toned torso, something that couldn’t be said of half the office on this floor. Sam sighed and settled back into his chair, pulling the end table over to use as a desk. Good thing he brought his textbooks.

It was halfway through the morning when Gabriel finally looked up at his new ‘employee.’ He was handsome, if way too serious, lost puppy, was a type. He couldn’t deny he was attracted to Sam, but attraction was just that, especially since there seemed to be no connection to go with it. Okay, that wasn’t true either, but the last time Gabriel had found someone this interesting, down to the crease in Sam’s forehead as he concentrated on his work, absentmindedly chewing on the end of a pen, it had ended horribly for everyone involved. There was a reason Gabriel was a sugar daddy and not a boyfriend. There was a reason why he would only be a sugar daddy and not a boyfriend. He would appreciate his time and his view with Sam while it lasted because Sam would do what they all do eventually: leave. And Gabriel was not going to be hurt when the time came.


	3. Kinks?

It was the weekend. The week had gone by all right, Sam only having to endure one day shirtless in Gabriel’s office like Mr. Milton had promised. Sam was working on an assignment in the living room when he heard the front door open. Funny. Gabriel-- Mr. Milton-- said he would be out honoring a commitment and wouldn’t be home today. Home. Sam had never really had a home before, but this house was so large that unless they were intentionally seeking each other out, he and Mr. Milton would never see each other.

He peeked out of the living room to see it was indeed Mr. Milton, wrapped around another man, entangled in a passionate kiss. He blinked, but instead of turning away, he leaned forward, cocking his head to the side. He had never thought of Gabriel like that, but seeing him like that… Sam was transfixed.

“Sam!” Mr. Milton saw him, pulling away from his partner. “I am so sorry, I forgot I—“

“It’s okay.” Sam said with a smile. “Carry on.” He ducked back into the other room, sneaking one last look to see Gabriel pull the taller man into a kiss, but watching Sam go. When Mr. Milton saw Sam watching still he had to duck to hide his smile. So the kid was interested even if he didn’t think he was. He’d test that theory.

“I could blow you right here.” He growled to his longtime friend, who smirked, knowing Gabriel well. He wasn’t a sugar baby, but since he preferred the loner lover life, he fit right in to Gabriel’s lifestyle and Gabriel fit right into his.

“If you wanna put on a show, you’ll have to prove it.” 

“Oh, Balth.” Gabriel smirked in return. Balthazar was the oldest by far, but stayed on because he also like the no strings attached sex they frequently partook of. “I love that you’re as filthy as me.”

“Corrupting the youth is what I’m about, baby.” Gabriel slipped down to his knees and Sam paused in his tracks. He hadn’t heard the conversation the two older men had, but he had a feeling that they were testing him. “Do you think we could convince him into a threesome?” Balthazar spotted Sam watching as Gabriel unbuckled his belt and pulled his tight jeans down. The boy looked so damn conflicted Balthazar took pity on him and winked, waggling his fingers at him.

“Softie.” Gabriel snorted, glancing over his shoulder to see Sam’s bright red cheeks disappear from sight.

“Now we wait to see if he’ll come back.” 

“Back room.” Gabriel stood up and tugged Balthazar waddling behind him into the back room by the front door. “Condom.” There were a lot of windows, enough to satisfy both of their kinks about being watched, even if Sam wasn’t interested. Balthazar pushes Gabriel back down to his knees and Gabriel obeyed, mouthing the Frenchman through his tight, black boxers. Today was a good day, a really good day.

Sam’s heart was pounding so loudly he was sure Gabriel and his guest could hear all the way at the front door. He couldn’t shake the image of Gabriel going to his knees, reaching to expose the other man. They had both been putting on a show for him, and he felt overwhelmed and intrigued all at the same time. He pressed a hand to the hardness in his jeans willing it to go away. He wasn’t like that. He wasn’t gay. This was just a job. It was just a natural reaction. It was like seeing live porn, he couldn’t help but react. He was alive after all. He’d have to be dead to not react to that, right? Ugh, he was going to need a cold shower or something.

Thankfully, his assignments pulled him back in and killed the boner he wasn’t supposed to have. He focused for the next twenty minutes or so until he had to use the bathroom. Of course, he had to pass by where he had left the two men, so he glanced around carefully to make sure the coast was clear. Thankfully, they seemed to have found Gabriel’s bedroom which Sam was relieved to realize. He slipped into the bathroom, locking the door behind him as he quickly relieved himself and washed his hands afterwards. When he came out, Balthazar was leaving, Gabriel not so much as walking him out. Frowning, Sam peered over by the front door to find Mr. Milton sprawled out on a daybed, a blanket haphazardly tossed over his form. 

“Sam,” he started up when he saw the younger man, “I am sorry. I forgot I promised you the house today. I ran into Balthazar after my appointment and well, we were never good at just standing around talking when there are other things we could be doing.”

“Is he a sugar baby?” Sam all but blurted the question burning on his tongue. 

“Balth? No, he’s an old friend with benefits.”

“You seem to have a lot of those.”

“Mmm.” Gabriel lifted up a bare shoulder in return, a far cry from the usually put together lawyer Sam was used to sharing the house with. It was intimate, seeing him with his hair mussed, lips pink, and the air smelling like… Sam flushed, realizing just how intimate this was, his inquiring after Mr. Milton’s lovers like it was any of his business. “It’s how I like it.”

“I’m sorry.” Sam ducked his head down. “It’s none of my business.” However, Mr. Milton wasn’t done and took his apology one step further.

“I’m also sorry for behaving inappropriately in front of you. Balthazar and I clearly made you uncomfortable and for that I am sorry.” Sam blinked in surprise.

“Okay.” He shrugged, avoiding looking at the older man as he swung around to leave the room. 

“And I’m sorry I’m basically naked right now. We might share a peeping Tom kink but I promise we can be well-behaved most days.” Gabriel grinned as Sam paused to glance back at him from the doorway. “I received bad news today and he was trying to show that he cares and that he wants to cheer me up the only way he knows how to.”

“Are you two dating?” Sam asked. “And are you okay?”

“No, dating would ruin our relationship.” Gabriel laughed. “I’m fine, thank you for asking. I think you’re going to be my only sugar baby at the rate I keep having people quit.”

“Someone other than Kevin?”

“Yea.” Gabriel pursed his lips. “Don’t worry, Sam, I’m used to people leaving. I’ve gotten quite good at saying good-bye.”

“That’s sad.” That slipped out before Sam could stop it, knowing a thing or two about people leaving or being forced to go. 

“It’s life.” Gabriel shrugged. “Go on, Samuel, I’m fine.” Sam grimaced and Mr. Milton smiled. He had learned that the name ‘Sammy’ was off limits, so he settled for calling Sam ‘Samuel’ when he wanted to tease him a little, which was almost all of the time. “I’ll get dressed once you go. I’ll shower and then be out of your hair as promised.” He watched as Sam self-consciously touched his hair before nodding, leaving the room quietly and quickly. He knew as much about Sam as Sam knew about him, and yet, while that was normally enough, Gabriel was curious. There had been understanding in Sam’s expression, understanding about people leaving. Who had left Sam? Gabriel found that he wanted to learn more about Sam, from Sam, and not some private investigator’s search. “Want to watch a movie tonight?” Gabriel called after Sam.

“Sure.” Sam called back, his voice echoing through the house. Gabriel settled back down on the daybed with a smile on his face. He’d rest a few more minutes before he got up and got dressed. It wasn’t every day he had a proper movie night lined up with his newest sugar baby.


	4. Omens

Sam stretched out on the couch, glancing up to see Mr. Milton was falling asleep. The movie had ended, the credits were rolling, and yet Sam had yet to move from his comfortable perch. He leaned back and curled around his pillow, very aware that the top of his head was brushing against the older man’s leg. He closed his eyes, listening to the soundtrack of the movie, enjoying the rare moment of peace. Moments like this, a moment like this, had been hard to find in his life.He was excited to find more in the near future. He and Mr. Milton had made plans for the weekend, plans to have a peaceful getaway. The other man had almost been shy about inviting him— it had been sweet, and so Sam had said yes.

His phone went off, jolting them both wide awake.

“I’m so sorry!” He stammered, grabbing his phone, yanking his old phone open. Mr. Milton watched him with amusement that Sam’s phone was an old flip phone. “Hello?”

“Sammy?”

“Dean? What’s wrong?”

“Does something have to be wrong?”

“Is something wrong?”

“It’s Mom.”

“What’s happened?” Sam cringed. The last thing anyone needed was his mother anywhere near Dean.

“She-- She found me. She saw me back at the store and followed me back to Bobby’s. She kept saying all her usual crap.”

“Why? I mean she kicked you out.”

“I know.” It was no secret that Dean had been their mom’s favorite when they were growing up. He had always taken more after her, while Sam took after their father. It didn’t win him any favors with their mother as her marriage to his father crumbled. And when she missed him terribly after the accident, well, Sam had been blamed for that too. But then Dean had come out, and suddenly Sam was their mother’s favorite and Dean was out on his own. Sam had to pretend to disown his own brother to keep a roof above his own head. It was their secret, still was, all those years ago. Now he was in college, being supported by his mother and brother, not feeling as if he deserved either of their support. Dean encouraged him to stay with their mother, just until he was out of school, and his mother assumed he had nothing to do with Dean, never bringing him up unless it was to profane his name and curse his existence. 

“Are you okay?”

“No!” Dean laughed. “I’m gonna go do what I do best, go drink, and then sleep this nightmare away. They say it gets better but let me tell you, it fucking gets worse.”

“Don’t say that. She’ll come around. And if she doesn’t… we don’t need her. You don’t need her. You don’t need that shit.”

“Sam, what would I do without you?” Sam hated that tone, the tone that reminded him he was all Dean had left and that he was probably letting him down like the rest of the family. He hated it because it reminded him of Jess who had always thought he wouldn’t amount to anything much without her. 

“Dean, you’re doing fine.” Sam replied. “You need to crash at the dorms?”

“No.” Dean sounded better now than when he first called. “I think it’s time I spread my damn wings, left mom and her drama behind. I’m moving to your town, Sammy!”

“That’s a big move. Mom visits too, you know.” She didn’t, but what if she did? Sam didn’t want to be responsible for anymore of his mother’s bigotry.

 

“So I’ll go to the town over. You’re the only family I have now, and I’d rather live near you.”

“Okay. It would be nice to have you closer.” Mr. Milton raised an eyebrow at that, scrolling through his phone like he wasn’t absolutely eavesdropping. He wondered who this Dean was. He sounded like a brother and he sounded like there was family drama in Sam’s life. Hmm. Gabriel sure knew a thing or two about that, though his had mostly settled into passive aggressiveness when they had to be around each other, marriages and funerals only usually.

“Yea! You can help me move this weekend, right?”

“You should wait two weeks.”

“No, I’m done.” Typical Dean, throwing himself headlong into whatever he thought his next course of action should be. “Bobby’s has been cutting my hours anyway. I don’t need their shit or mom’s anymore.”

“I can’t help this weekend.”

“Why not?”

“I’m going on a trip.”

“I thought you were too broke for that. Oh, Sammy,” Dean’s tone became teasing and Sam cringed, “you haven’t started working a corner have you?”

“What?! No!” Sam recoiled. “It’s with a friend, even though that is none of your business.”

“Since when do you have friends?” Dean snorted. “You don’t have to lie if you don’t want to help me.”

“It’s not that. I’ll help you on Monday.”

“Uh huh, sure, I want to meet whoever is so important that you can’t help your brother move.”

“Dean, you don’t even have a place.”

“Yes I do.”

“What?”

“So I’ve been looking for a while.” Dean confessed. “I got a place a while ago, and it’s available starting this weekend for me to move into.”

“Why didn’t you tell me sooner?!”

“I wanted to surprise you.”

“You certainly have.” Sam said weakly.

“I’m going to need a little help with rent though…”

“Dean.” Sam rolled his eyes. “Get a job.”

“I don’t start until next week.”

“Fine.” Sam sighed. “And I’ll help you on Monday.”

“Don’t patronize me.” Dean teased. “Love you, bitch.” He clicked end before Sam could even respond.

“Everything okay?” Sam looked up to see Gabriel watching him intently.

“I don’t know if I can go this weekend. I want to, but family shit came up.”

“Which one would you rather do?”

“Go with you.” Sam didn’t know why he was blushing. It was just a simple trip. For crying out loud, he was getting paid for the weekend away. Gabriel huffed, mollified by the answer, but also not wanting to lose his weekend with Sam. “I feel bad though.”

“It sounded like they were making you feel that way.”

“Yea.” Sam replied. “But I’m all they have.”

“Well, maybe they need to make some friends.” Gabriel winced, recognizing his tone wasn’t how it should sound.

“You don’t even know him.”

“I’m sorry.” Gabriel backtracked, apologizing diplomatically. “You’re right. I don’t. I will keep my nose out of your family affairs.” Sam snorted, but there was amusement instead of derision playing across his face.

“Oh, you really are a lawyer.”

“Researching me I see.” Gabriel smiled, coaxing a smile out of Sam in turn.

“I wanted to know what I was getting myself into.” Sam replied cheekily, much to Gabriel’s delight. Mr. Milton was definitely easier to talk to now that they had been living together for a short while. Too easy. Sam knew he probably shouldn’t feel so comfortable around him. If his luck was anything like his family’s, nothing good would come out of it.

“If you can’t make the trip, we can go next weekend.” Gabriel offered. “I can postpone.”

“Won’t you lose money?” 

“I know the owner.” Gabriel shrugged. “I’ll just ask her to move the dates.”

“I’d like that.” Gabriel’s thoughtfulness was rewarded with a dimple. “Thanks for understanding.” Gabriel smiled back, feeling oddly pleased with himself and not entirely sure why. Nothing good could come out of these… feelings… that was for sure. He couldn’t let Sam end up like Ezekiel.


	5. Snap, Crackle, and Pop

Sam thought it was silly that he was dragging his feet at the thought of helping Dean moved. He loved his older brother and he needed to be there for Dean like Dean had always been there for him.

“Here.” Gabriel handed him a wrapped box.

“What’s this?”

“I got you something.”

“Why?” Sam laughed. “I’m ditching you this weekend, remember?”

“Maybe I want to make sure you think of me while you’re away.” Gabriel said flirtatiously.

“It’s not like I can forget you that easily.” The remark slipped of Sam’s tongue far too easily and he realized why he didn’t want to see Dean today. He didn’t want Dean to know about Gabriel. He didn’t want Dean to think there was something going on, and he especially didn’t want Dean to know Gabriel was paying him to—to— whatever Gabriel was paying him to do.

“What’s wrong?” Gabriel noticed how Sam’s face fell.

“Nothing.” Sam shook his head.

“Open your present.” Gabriel reminded him. “You can sulk when you’re with your brother.” Sam huffed out a response but obeyed, peeling back the wrapping paper.

“Gabriel!”

“Do you like it?” It was a brand new iPhone, the latest release. Sam had seen articles about people lined up around the block for these and here he had one in his hand.

“It’s too much.” Sam protested, but he was already staring down at the shiny screen with a soft smile on his lips. He had always wanted one, made it out like he didn’t, but he had. And Gabriel had given him one. He put the phone down gingerly and stepped over to Gabriel quickly, wrapping him in an impromptu hug. “Thank you. I love it.” He realized the awkwardness a moment too late, stepping back and releasing Gabriel. “Sorry.” A dimple flashed even as his cheeks flushed. “I just really appreciate this. I’ve always wanted an iPhone, silly, I know.”

“I don’t think it’s silly.” Gabriel smiled, tilting his head to the side. “I’m glad you called me, Sam.” They were both silent, one thinking about the first day they met and the other still staring in shock and joy at his new phone. “Now go see your brother. Call me if you need anything. I took the liberty of adding my number. It’s under ‘Hottest Sugar Daddy Ever.’”

“Of course it is.” Sam snorted. “Thank you again.”

“Pish posh.” Gabriel waved him on. “Bye, Sam.”

“Bye, Gabriel.” Sam did a little wave, scooping his new phone up carefully. Gabriel handed him the case he had bought for the weekend. 

“We can go shopping for a new one when you get back. I just didn’t want it to get broken on you the first two days you had it.”

“Thanks.” Sam was flustered but in a good way. This was not what he expected when he had called Gabriel Milton looking for a job. He was not used to all of this, but it was so nice if he was being honest. Being around Gabriel was nice too if he was being honest. Maybe that was why he didn’t want to see Dean. Dean would question just why it was so nice and Sam didn’t want Dean to think he was gay. Sam didn’t want to think about that any more. “Bye, Gabriel.” He called over his shoulder and shut the front door behind him. He walked to the taxi he had called and got in, giving the driver his old address. Dean wouldn’t be in for another hour or so, but Sam wanted to get there ahead of him. He didn’t want Dean to know about Gabriel. Dean would want to know everything, and he’d ask Sam for more money than he was already asking for. Sam couldn’t let that happen. He needed the money he was earning having fun with Gabriel and well, he wanted to keep this one nice thing in his life to himself.

Gabriel watched Sam go, shaking his head. He needed to pull himself together. He was failing miserably at not getting attached. And he had to go ahead and buy Sam another expensive gift. He was always upset that people stayed around to use him and his money and here he was, setting his and Sam’s relationship up the way he did with everyone else. No wonder he was alone. He was way too good at self-sabotaging. He would enjoy Sam’s company, take whatever the young man was willing to give, and when Sam decided to leave them like they all always decided to do, he would self-medicate like he always did with someone new and maybe a bottle of whiskey too.

“Dean.” Sam got out of the taxi, handing the driver his fare. “You’re here early.” Dean slid out of the Impala with a scowl. The taxi driver looked at the two of them and drove off a little faster than was necessary.

“What the fuck, Sam? I already talked to your landlady. She said you left like a month or so ago.”

“I did.” Sam heard himself saying. “I couldn’t live here anymore. I didn’t make enough and it wasn’t worth what I was paying.”

“I busted my ass off to get you that apartment in the first place.”

“I’ll pay you back!” Sam yelled.

“Geez, Sam, are you even living anywhere? You’re not homeless, are you?”

“I’m staying with some friends right now.” Sam answered semi-truthfully. Honestly, he and Gabriel could probably become great friends if they kept at the pace they were going. “They’re helping me out.”

“Why?”

“Actually, the school connected us. They work in the field and do some amazing stuff, so it’s like a weird shadow program.” 

“That’s cool.” Dean said. “It’s also exactly opposite of what you just said. Which is it, Sam?” Sam flushed, squirming as he was caught in his lie. He squared his shoulders and decided to give it to Dean straight.

“It’s a friend. They’re giving me work and letting me live with them. They really are a lawyer, but the school didn’t connect us, a friend from school did, someone who used to work for them.”

“Doesn’t sound like a friend.”

“They’re my employer, but they’re also a good person, Dean. We’re becoming friends. Living with people does that occasionally.”

“Huh, maybe mom and I should try it sometime.” Dean joked. “They fucking you?”

“Dean!”

“What?” Dean gave him an innocent look. “You have new clothes, expensive clothes, I see the new iPhone peeking out of your pocket… you can’t tell me they’re paying you that much.”

“They have high standards.” Sam said defensively. 

“Definitely fucking.” Dean smirked.

“I am not having sex with him!” 

“Him?” Dean pounced on that bit of information. “So you’re staying with a male lawyer who is giving you free, expensive shit, but not for sex… Sam, where’d you land the sugar daddy?” He teased. Sam groaned in frustration.

“You can move yourself.” He snapped, tossing an envelope at Dean. “There’s my help for rent.”

“Don’t get your boxers all twisted…”

“Leave me alone!” Sam snarled. “You have no idea how bad it’s been, how desperate I was to even go to this guy for the job. I’m lucky he’s kind, decent, and thoughtful, I know that, but you don’t get to fucking laugh at me like you know what it’s been like.” Sam shivered a little, straightening himself up. “I’m going home and I’m going to forget this shit ever happened. I have homework to do.”

“Oh my god.” Dean covered his laugh with his hand. “He fucking in your sugar daddy. I was just joking. Sam, I’m sorry, you could have told me things were that bad.”

“I’m sick of being a burden to you and mom.” Sam mumbled. But he had stopped walking away. He had yet to turn around but he had at least stopped. Dean hurried over and pulled his little brother into a big hug.

“You are never a burden, Sammy. This guy treating you right?”

“Yea. He’s really nice.”

“Yea? You got a little crush?”

“Dean.” Sam gritted his teeth. “I’m not—“

“Chill, Sam, I am, remember? Hey, is he hiring at all?” Dean pulled back, giving Sam a lascivious grin.

“Not that I know of.” Sam lied, shaking his head. He would not share Gabriel with Dean. He wouldn’t. Gabriel was his! Well… not like that… 

“I think it’s so funny you’re all flustered, Sammy. It’s okay to like dudes too. Besides, they’re better at giving head.” Unbidden, the memory of Gabriel dropping to his knees, pulling down Balthazar’s underwear popped up in Sam’s mind. He flushed, shifting away from his brother.

“Gross, Dean.” But he couldn’t ignore the flicker of arousal that memory had awakened. Whatever this was, it had to be unique to Gabriel, right? Sam’s mom would freak if he was gay too. Okay, okay, nothing was going on with him and Gabriel. Gabriel was his employer and well on his way to being considered a friend. Sam felt safe and cared for around him and for Sam, that meant a lot.

“Come on, Sammy. Let’s go get some coffee and start the day over.” Dean led the way to the Impala. “I can’t wait to show you my place after. It’s pretty nice and my roommate’s not bad. He’s a little weird, but he prefers to keep to himself.”

“Okay.” Sam was relieved the day seemed to be turning around. He didn’t know why he always got so tense when he knew he was going to see his family. Maybe it was all the fighting. Whatever it was, he knew he was part of the problem. He just didn’t know how to stop.

**Notes for the Chapter:**

> Hey all,
> 
> Sorry for my unplanned sabbatical. The last story I was working on kind of got to me, not in a good way, so I deleted it, but I just couldn’t write for a while. But I’m back and slowly working through life. Hope you all like this new chapter!
> 
> -fluffy


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